Tag: M.W=100-200

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 10485-09-3, name is 2-Bromoindene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Bromoindene

A 2.02 g (83.1 mmol) piece of magnesium was charged into a sufficiently dried and argon-replaced 200 mL reactor, and stirred vigorously while heating under reduced pressure for 30 minutes.Cool to room temperatureAfter that, a piece of iodine and 25 mL of tetrahydrofuran were charged and stirred. A 20 mL dilute solution of 3.92 g (20.1 mmol) of 2-bromoindene in 20 mL of tetrahydrofuran was slowly added, and the mixture was heated to reflux in an oil bath at 80 C. for 1 hour.This reaction solution was slowly added to a solution of 12.0 mL (100 mmol) of dimethylsilyldichloride in 10 mL of n-hexane under cooling with cooling, and stirring was continued for 18 hours while returning to room temperature.After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 20 mL of tetrahydrofuran and 1.90 mL (20.2 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue.9.79 g of n-butylcyclopentadiene solution (25 wt% of tetrahydrofuran solution, 20.0 mmol) and 20 mL of tetrahydrofuran are charged into a sufficiently dried, argon-substituted 100 mL reactor, and 12.5 mL of n-butyllithium solution (hexane solution) , 1.60M, 20.0 mmol) was added and stirred at room temperature for 2 hours.This solution was added dropwise to the previously diluted reaction residue diluted solution cooled to -78 C., and stirring was continued for 17 hours while gradually returning to room temperature.Saturated aqueous ammonium chloride solution was added, the soluble matter was extracted with n-hexane, the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate.After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the target compound represented by the following formula (AL) (hereinafter referred to as compound (AL)) Was obtained as an isomer mixture of 4.65 g (yield 79%).

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsui Chemicals Chemicals company; Tanaka, Kenichi; Harada, yasuyuki; (44 pag.)JP2019/69920; (2019); A;,
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Electric Literature of 74586-53-1, The chemical industry reduces the impact on the environment during synthesis 74586-53-1, name is 3-Bromo-5-methylaniline, I believe this compound will play a more active role in future production and life.

INTERMEDIATE 8: N-[3-methyl-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenyl]-4- (trifluoromethyl)pyrimidin-2-amineStep 1 : A solution of 3-bromo-5-methylaniline (162.5 g, 873.66 mmol) in 1,4-dioxane (2 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (182 g, 994.54 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated in vacuo. The residue was diluted with 2 L of water, then adjusted to pH 7-8 with aqueous saturated sodium bicarbonate solution, followed by extraction with EtOAc (2×2 L). The organic layers were combined, washed with water (2x 2 L), dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-(3- bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS ESI calc’d for Ci2H,oBrF3N3 [M + H]+ 332, 334, found 332, 334. NMR (400 MHz, CDCI3): delta8.68 (d, J= 4.9 Hz, 1 H), 7.79 (s, 1 H), 7.33-7.23 (m, 2 H), 7.10-7.06 (m, 2 H), 2.36 (s, 3 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; ELLIS, John Michael; FISCHER, Christian; GRIMM, Jonathan; HAIDLE, Andrew, M.; KATTAR, Solomon, D.; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETROCCHI, Alessia; SCHELL, Adam, J.; ZHOU, Hua; WO2012/154519; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7745-91-7, name is 3-Bromo-4-methylaniline, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7745-91-7, Recommanded Product: 7745-91-7

Methyl chloroformate (0.202 ml, 2.62 mmol) was added to a solution of 3-bromo-4-methyl-phenylamine (243 mg, 1.31 mmol) in pyridine (2 ml), and the mixture was stirred at room temperature overnight. H2O was added to the reaction mixture, followed by extraction with AcOEt (x 2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-hexane/AcOEt) to give (3-bromo-4-methyl-phenyl)-carbamic acid methyl ester (288 mg, 90%). 1H-NMR (270 MHz, CDCl3) delta 2.34 (3H, s), 3.77 (3H, s), 6.51 (1H, br. s), 7.14 (1H, d, J = 7.2 Hz), 7.20 (1H, dd, J = 7.4, 2.0 Hz), 7.63 (1H, d, J = 2.0 Hz).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; EP2433940; (2012); A1;,
Bromide – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 10269-01-9 as follows. 10269-01-9

A solution of (3-bromophenyl)methanamine (1 g, 5.37 mmol) in dichloromethane (10 mL) at 10 C. was treated with triethylamine (1 .498 mL, 10.75 mmol) then fe/ -butyl dicarbonate (1 .498 mL, 6.45 mmol) and stirred at 10 C for 4 h. Water (10 mL) was added then the mixture extracted with DCM (2 x 10 mL), washed with brine, dried and evaporated and the residue purified by chromatography (silica gel, 10:1 hexanes/ethyl acetate) to afford the desired product (1 .5 g; 93%) as a colorless solid. NMR (500 MHz, CDCI3) delta ppm 7.43 (s, 1 H), 7.39 (d, J = 6.8 Hz, 1 H), 7.20 (d, J = 6.8 Hz, 2H), 4.89 (s, 1 H), 4.29 (d, J = 5.7 Hz, 2H), 1 .46 (s, 9H).

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DUFFY, Kevin J.; PARRISH, Cynthia Ann; ATOR, Laura E.; BASKARAN, Subramanian; DARCY, Michael Gerard; OPLINGER, Jeffrey Alan; RALPH, Jeffrey M.; RIDGERS, Lance Howard; TIAN, Xinrong; ZHANG, Cunyu; (225 pag.)WO2019/53617; (2019); A1;,
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583-75-5, These common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

3,6-Dibromotoluene In a 2000 ml beaker containing 400 ml of 23percent aqueous HBr, 46.5 g (0.25 mol) of melted 2-methyl-4-bromoaniline was slowly added. This mixture was stirred for 20 minutes using a mechanical stirrer, then cooled to -5¡ã C. Then a solution of 22.4 g (0.33 mol) of NaNO2 in 130 ml of water was added dropwise over 1 hour at this temperature. The diazonium reagent obtained was added in several portions to a solution of 35.9 g (0.25 mmol) of CuBr in 100 ml of 47percent HBr at 0¡ã C. The resulting mixture was warmed to 70¡ã C., stirred for 30 minutes at this temperature, and, then, cooled to room temperature. The product was extracted with 3*200 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. Firstly, the crude product was purified using short column with Silica Gel 60 (40-63 mum, d 60 mm, 140 mm; eluant: hexanes). Fractional distillation gave colorless oil, b.p. 100-102¡ã C./10 mm Hg. Yield, 36.1 g (58percent). Anal. calc. for C7H6Br2: C, 33.64; H, 2.42. Found: C, 33.79; H, 2.50. 1H NMR (300 MHz, CDCl3): delta 7.39 (m, 1H, 5-H), 7.37 (m, 1H, 3-H), 7.18 (m, 1H, 6-H), 2.38 (s, 3H, Me). 13C NMR (75 MHz, CDCl3): delta 139.9, 133.6, 133.5, 130.3, 123.5, 120.9, 22.7.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 583-75-5.

Reference:
Patent; Voskoboynikov, Alexander Z.; Izmer, Vyatcheslav V.; Asachenko, Andrey F.; Nikulin, Mikhail V.; Ryabov, Alexey N.; Lebedev, Artyom Y.; Coker, Catalina L.; Canich, Jo Ann M.; US2007/135597; (2007); A1;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-fluoroaniline, molecular formula is C6H5BrFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 65896-11-9

General procedure: To a solution of o-haloaniline (4.63 mmol) in dry DCM (20 mL) at room temperature was dropped acyl chloride (5.09 mmol). The reaction mixture was stirred for 24 hours then poured into water, extracted with DCM, washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The product was carried on to next step without any further purification in most cases.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65896-11-9, its application will become more common.

Reference:
Article; Shi, Yajie; Zhou, Qifan; Du, Fangyu; Fu, Yang; Du, Yang; Fang, Ting; Chen, Guoliang; Tetrahedron Letters; vol. 60; 40; (2019);,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1252934-30-7, name is 3-(Bromomethyl)-1,1-difluorocyclobutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1252934-30-7

Ethyl (R)-12-hydroxy-l l-methoxy-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l- a]pyrrolo[l,2-c]phthalazine-7-carboxylate (59 mg, 150 muetaiotaomicron) was combined with 3- (bromomethyl)-l,l-difluorocyclobutane (85 mg, 460 mumol) and Potassium Carbonate (85 mg, 0.61 mmol) in DMF (0.4 mL). The mixture was stirred at 70 C for 55 minutes, and then cooled to room temperature. Aqueous 1M lithium hydroxide (334 mu) was added and the mixture was stirred at 35 C for 30 minutes. The mixture was cooled to room temperature, diluted with TFA, and purified by preparative HPLC to provide (R)-12-((3,3-difluorocyclobutyl)methoxy)-l l- methoxy-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7- carboxylic acid as a TFA salt. l NMR (400 MHz, Acetonitrile-d3) delta 8.45 (s, IH), 7.39 (s, IH), 7.26 (s, IH), 6.95 (d, J = 0.9 Hz, IH), 4.84 (d, J = 6.2 Hz, IH), 4.16 (qt, J = 12.8, 6.5 Hz, 2H), 3.92 (s, 3H), 2.85 – 2.33 (m, 7H), 1.89 (ddd, J = 12.6, 7.8, 2.7 Hz, IH), 1.62 (ddd, J = 12.4, 10.8, 7.8 Hz, IH), 1.36 (s, 3H), 0.66 (s, 3H). 19F NMR (376 MHz, Acetonitrile-d3) delta -77.33 , -84.17 – -85.00 (m), -93.89 – -94.83 (m). MS (m/z) 461.3 [M+H]+.

The synthetic route of 1252934-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CANALES, Eda; CURRIE, Kevin S.; KATO, Darryl; LI, Jiayao; LINK, John O.; METOBO, Samuel E.; SAITO, Roland D.; SCHROEDER, Scott D.; SHAPIRO, Nathan; TSE, Winston C.; WU, Qiaoyin; (262 pag.)WO2018/144605; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-fluoroaniline, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 656-64-4, 656-64-4

N-Hydroxy-4-((2-methoxyethyl)amino)-1,2,5-oxadiazole-3-carbimidoyl chloride (1.5 kg, 6.8mol) was mixed with water (10 L). The mixture was heated to 60C. 3-Bromo-4-fluoroaniline (1.44 kg, 7.46 mol) was added and stirred for 10 mm. A warm sodium bicarbonate (0.86 kg, 10 mol)solution (10 L water) was added over 15 mm. The reaction mixture was stirred at 60C for 20 mm. The reaction mixture was cooled to room temperature and extracted with EtOAc (10 L*2). The combined organic solution was dried over sodium sulfate and concentrated to give the desired product (2.3 kg, 90%) as a brown solid. LCMS (M + H) : m / z = 374.0, 376.0. 1H NMR (400MHz, DMSO-d6): 6 11.55 (s, 1H), 8.85 (s, 1H), 7.16 (t, J = 8. 8Hz, 1H), 7.08 (dd, J = 6.1, 2.7Hz, 1H), 6.75 (m,1H), 6.14 (t, J = 5.8Hz, 1H), 3.48 (t, J = 5.2Hz, 2H), 3.35 (dd, J = 10.8, 5.6Hz, 2H), 3.22 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; KAZMIERSKI, Wieslaw Mieczyslaw; DE LA ROSA, Martha; SAMANO, Vincent; (70 pag.)WO2017/2078; (2017); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 17247-58-4, 17247-58-4

4e. Preparation of cyclobutylcarbinylsulfonamide A solution of 12.3 g (83 mmol) of cyclobutylcarbinyl bromide (Aldrich) and 13.7 g (91 mmol) of sodium iodide in 150 mL of acetone was refluxed overnight and then cooled to room temperature. The inorganic solids were filtered off and the acetone and cyclopropylcarbinyl iodide (8.41 g, 46%) distilled off at ambient and 150 torr at 80 C., respectively. A solution of 4.0 g (21.98 mmol) of cyclobutyl carbinyl iodide in 30 mL of anhydrous diethyl ether (diethyl ether) cooled to -78 C. was cannulated into a solution of 17 mL (21.98 mmol) of 1.3M sec-butyllithium in cyclohexanes and the solution was stirred for 5 minutes. To this mixture was cannulated a solution of 3.0 g (21.98 mmol) of freshly distilled sulfuryl chloride in 110 mL of hexanes cooled to -78 C., the mixture warmed to room temperature over 1 hour and was then carefully concentrated in vacuo. This mixture was redissolved in diethyl ether, washed once with some ice-cold water, dried (MgSO4), filtered, and concentrated carefully. This mixture was redissolved in 30 mL of THF, added dropwise to 500 mL of saturated NH3 in THF and was allowed to stir overnight. The mixture was concentrated in vacuo to a crude yellow solid and was recrystallized from the minimum amount of dichloromethane in hexanes with 1-2 drops of methanol to afford 1.39 g (42%) of cyclobutyl carbinylsulfonamide as a white solid. 1H NMR (CDCl3) delta 1.81-2.03 (m, 4H), 2.14-2.28 (m, 2H), 2.81-2.92 (m, 1H), 3.22 (d, J=7 Hz, 2H), 4.74 (brs, 2H); 13C NMR (CDCl3) delta 19.10, 28.21, 30.64, 60.93; MS m/e 148 (M-1)-. time: 1.73, method B), 818 (M++H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (Bromomethyl)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sin, Ny; Good, Andrew Charles; Venables, Brian Lee; Scola, Paul Michael; Meanwell, Nicholas A.; US2006/183694; (2006); A1;,
Bromide – Wikipedia,
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65896-11-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 65896-11-9 as follows.

To a suspension of sodium perborate tetrahydrate (135.374 g., 886.4 mmol) in 500 mL acetic acid at 55 C. was added dropwise a solution of 2-bromo-6-fluoro-phenylamine (33.685 g., 177.271 mmol) in 70 mL acetic acid over 1 hour. The reaction mixture was stirred at 55 C. for an additional 3 hours, then cooled to 0 C. in an ice bath. Insoluble materials were removed by filtration through a plug of celite, which was rinsed with 100 mL acetic acid. The combined acetic acid fractions were added to 3 L ice water with stirring to give a waxy solid which was removed by filtration. The crude solid was dissolved in 250 mL ethyl acetate, washed three times with 200 mL of 10% aqueous hydrogen chloride, 200 mL saturated sodium bicarbonate and 100 mL brine. The solution was concentrated in vacuo to give 11.51 g of 1-bromo-3-fluoro-2-nitro-benzene as a red oil, 1H NMR (CDCl3, 300 MHz) delta: 7.26 (m, 1H), 7.38 (m, 1H), 7.49 (m, 1H)

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2007/15744; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary